Hydrochloric Acid → 2-Hydroxy-succinic acid 4-(4-allyl-2-methoxy-phenyl)ester

HRID 82495

Reaction equation

HRID 82495 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:21])[CH2:12][CH:13]2[C:17](=[O:18])[O:16]C(C)(C)[O:14]2)=[C:6]([O:22][CH3:23])[CH:5]=1)[CH:2]=[CH2:3].Cl>C1COCC1>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:21])[CH2:12][CH:13]([OH:14])[C:17]([OH:18])=[O:16])=[C:6]([O:22][CH3:23])[CH:5]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67346743(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid 4-allyl-2-methoxy-phenyl ester

Product 1

HCID 673255242-Hydroxy-succinic acid 4-(4-allyl-2-methoxy-phenyl)esterYield 107%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid 4-allyl-2-methoxy-phenyl ester (35.0 g, 0.10 mol) in THF (350 mL) was added 1N hydrochloric acid (350 mL) at room temperature (25° C.) and the mixture was stirred at same temperature over a period of 8 h. The solvent was evaporated to half volume, saturated with sodium chloride and the product was extracted with ethyl acetate (2×850 mL). The organic layer was dried over sodium sulphate and concentrated to obtain off-white solid (30.0 g, 98%).

Workup

  1. customThe solvent was evaporated to half volume, saturated with sodium chloride
  2. extractionthe product was extracted with ethyl acetate (2×850 mL)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-eccb2e7a26404c4fb4770b967608d66d
Source dataset
uspto-grants-2014_09
Patent number
US08846721B2

Linked notes

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